系統識別號 | U0002-1108201514373400 |
---|---|
DOI | 10.6846/TKU.2015.00277 |
論文名稱(中文) | 具筒型之鉑金屬盤形雙聚物、及一、二和三取代之炔吡啶基多炔苯基苯與具手性之環碳酸化筒型化合物的液晶及光學性質研究 |
論文名稱(英文) | The Mesogenic and Optical Properties of Platinated Discotic Dimers and Multi-phenylethylbenzenes with Mono-, Di-, and Tri-pyridylethynyl Groups and Cyclic Carbonate-based groups |
第三語言論文名稱 | |
校院名稱 | 淡江大學 |
系所名稱(中文) | 化學學系博士班 |
系所名稱(英文) | Department of Chemistry |
外國學位學校名稱 | |
外國學位學院名稱 | |
外國學位研究所名稱 | |
學年度 | 103 |
學期 | 2 |
出版年 | 104 |
研究生(中文) | 廖竟婷 |
研究生(英文) | Ching-Ting Liao |
學號 | 897160023 |
學位類別 | 博士 |
語言別 | 英文 |
第二語言別 | |
口試日期 | 2015-06-29 |
論文頁數 | 163頁 |
口試委員 |
指導教授
-
徐秀福
委員 - 賴重光 委員 - 山田徹 委員 - 施增廉 委員 - 梁蘭昌 委員 - 吳俊弘 |
關鍵字(中) |
盤形向列型 筒型液晶 熱致型 溶致型液晶 鉑金屬雙聚物 前鋒軌域理論 炔吡啶基 多炔苯基苯 環碳酸化反應 偏光顯微鏡 熱微差掃描分析儀 粉 末X 光繞射 圓二色光譜儀 |
關鍵字(英) |
platinated-metallomesogenic dimers nematogenic pyridyl pyrazolate ligands chromophores thermotropic lyotropic pyridyl titration cyclic carbonated negative cotton effect |
第三語言關鍵字 | |
學科別分類 | |
中文摘要 |
本論文分為四個章節,第一章以鉑金屬為中心金屬連接兩個pyridyl pyrazolate 配位基形成雙聚物,此系列以代號Ptdax 表示,x 代表不同碳鏈長度。利用偏光顯微鏡、熱微差掃描分析儀及粉末X 光繞射確認此系列化合物均具有筒型液晶相,液晶溫度範圍大於250 oC 且其熱烈解溫度均高達340 oC。第二章仍以鉑金屬為中心金屬,連接兩個五炔苯基苯盤形單元。此系列以代號Pt1cx 及Pt1ocx 表示,cx 代表不同烷鏈碳鏈長度,ocx 代表不同烷氧鏈碳鏈長度。以系列化合物皆具有盤形向列型液晶相,具烷鏈鉑金屬雙聚物熱性質穩定。此外,化合物Pt1oc4 單晶繞射結果顯示具烷氧鏈鉑金屬雙聚物整體分子平面性較好,因此粉末X 光繞射得到此類分子具有較大範圍排列的結果。第三章中分子設計以一個多炔苯基苯為主體,分別接上不同數量的炔吡啶基。利用推拉電子基效應使分子中具有拉電子基的官能基其電子密度分部落在前鋒軌域理論的LUMO,而具有推電子基的官能基其電子密度分部落在前鋒軌域理論的HOMO,利用此分子設計的差異在不同酸性、不同金屬及溶劑條件下研究液晶及光學性質。此系列以代號1N1,x、2N1,x、3N1,x 及3N2,x 表示,x代表不同碳鏈長度。結果顯示此系列化合物隨著碳鏈及炔吡啶數目不同而產生盤形向列型或筒型液晶相。此外,利用偏光顯微鏡及粉末X 光繞射結果證實化合物1N1,12 具有熱致型及溶致型液晶性質;此化合物溶於四氫伏喃(THF)溶劑中後再加入W6+及Pd2+金屬,造成強消光現象且Pd2+金屬還造成20 nm 的紅位移,證實化合物1N1,12 對此兩金屬有專一性。化合物1N1,12 及3N1,12 在2.0 當量的三氟乙酸中皆產生強消光現象,且兩化合物在具有相同當量的三氟乙酸中產生不同顏色,推測上述結果來自於分子設計造成不同的的電子密度分布而產生。第四章部分,利用日本慶應大學山田徹老師實驗室發展出的銀金屬催化系統利用添加二氧化碳進行環碳酸化反應而形成高純度旋光性化合物反應,在本實驗室發展出的五炔苯基苯盤形單元上進行Sonogashira 反應而形成具有室溫筒型液晶性質的化合物C2oc8。另一化合物EC2oc12 在圓二色光譜儀實驗中發現具有負型卡頓效應(Cotton effect)。 |
英文摘要 |
The thesis contains four chapters. In chapter one and two, we investigated the influence of the molecular packing of discotic platinated-metallomesogenic dimers on their mesogenic and optical properties, especially their photo-luminescent studies. In chater one, a platinum chelated pyridyl pyrazolate ligands to form a square planar structure. The molecular design led the compounds possessed wide mesogenic temperature range (> 250°C) and achieved mesomorphically stable (Td > 340 °C). In chapter two, a spacer with platinum moiety bridged two discotic pentaynylethylbenzenes. The Pt1oc6 possessed wide nematogenic temperature range (> 130°C). Being compared with Pt1c4, the more planar structure of Pt1oc4 possessed longer molecular packing length found in the results of powder X-ray diffraction investigation. This indicated that the alkoxy chains potentially helps Pt1oc4 to achieve large domain alignment. In chapter three, the molecular design concept based on adding donor and/or acceptor substituents to the chromophores at suitable positions resulted in separately electronic shifts in HOMO and LUMO into opposite directions. The discotic monopyridyl derivatives, 1N1,12 possessed both thermotropic and lyotropic properties. The 1N1,12 behaved as a enantiotropic liquid crystal and achieved room temperature Smactic C phase. Another tripyridyl derivative, 3N1,12 possessed columnar phase. The fluorescent investigation results showed that 1N1,12 quenched almost all d8 metal ions and K+, Hg2+, Pd2+, V5+, and W6+. However, the 3N1,12 quenched only Cu2+, Hg2+, Pd2+, and W6+ metal ions. Besides, to titrate with tetrafluoric acid (TFA) from 0.5 to 2.0 equivalents, the emissive intensity decrease seriously. Both of the optical results indicated that the discotic-pyridyl derivatives could be tuned by the designed electronic distribution to bind individual metal ions and to manipulate the appeared colors in varied pH values. In the last chapter, a series of cyclic carbonated moiety attached on pentaphenylethylbenzene were synthesized. A room temperature (C2OC8) columnar mesogens were achieved. The CD investigatino of EC2OC12showed negative cotton effect. |
第三語言摘要 | |
論文目次 |
Chapter 1…………………………………….………………………………………..1 Investigation of Mesogenic and Optical Properties of Platinum(II) Complexes with Tris(alkoxy)phenyl-Functionalized Pyridyl Pyrazolate chelates…….......…..1 1-1 Introduction…………………………………………………………………..2 1-2 Experimental Section…………………………………….…………………4 1-3 Results and Discussion……………………………………………………..4 Solid state structure studies of Single Crystal X-ray investigation…………4 Thermal properties of series Ptdax…….....…………………………………5 Powder X-ray Diffraction study of series Ptda…………………………………..6 Optical Properties of series Ptdax………………………………………………11 1-4 Conclusions…………………………………………………………………….15 1-5 References………………………………………………………………………16 Chapter 2………………………………………………………………...………….23 Investigation of Mesogenic and Optical Properties of Discotic Nemetogens Dimers Bridged with Pt(PEt3)2 Moiety……………………….......………….23 2-1 Introduction…………………………………………………….……………….24 2-2 Experimental section………………………………………………………26 2-3 Results and Discussion………………………………………………………….40 Mesogenic Properties…………………….……………………..………………..40 Powder X-ray Diffraction (PXRD) Investigation……………….……………….46 Adsorption and emission properties in solution………………….………………53 2-4 Conclusions………………………………………………..…………………….59 2-5 References……………………………………………………………………….60 Chapter 3…………………………………………………………………………..58 Investigation of Mesogenic and Optical Properties of Multi-phenylethylbenzenes with Mono-, Di-, and Tri-pyridylethynyl Groups……………………………....58 3-1 Introduction…………………………………………………………..……….59 3-2 Experimental section…………………………………………………………..61 3-3 Results and Discussion…………………..…………………………………….86 Mesogenic Properties……………………………………………...……………..86 Investigation of Lyotropic Liquid Crystal Properties…………...………………101 Powder X-ray Diffraction (PXRD) Investigation…………….……...…………105 Optical Properties of 1N1,12……………………………………………...……...122 Optical Properties of 1N3,12……………………………………………...……...129 3-4 Conclusions…………………………………………………...………………..137 3-5 References…………………………………...……………...………………….138 Chapter 4……………………………………………………………………….….144 Room temperature chiral columnar liquid crystals by the generation cyclic carbonate moiety with a chiral center onto pentaphenylethy-lbenzene………………………..144 4-1 Introduction…………………………..………………………………………..145 4-2 Experimental Section………………………………………………….………150 4-3 Results and Discussion………………………………………………..……….154 Synthesis……………………………………………………………….………..154 Mesogenic Properties…………………………………………………...………157 4-4 Conclusions…………………………………………………………………….161 4-5 References…………………………………………..………………………….162 Powder X-ray Diffraction (PXRD) Investigation…………….……...…………105 Optical Properties of 1N1,12……………………………………………...……...122 Optical Properties of 1N3,12……………………………………………...……...129 3-4 Conclusions…………………………………………………...………………..137 3-5 References…………………………………...……………...………………….138 Chapter 4……………………………………………………………………….….144 Room temperature chiral columnar liquid crystals by the generation cyclic carbonate moiety with a chiral center onto pentaphenylethy-lbenzene………………………..144 4-1 Introduction…………………………..………………………………………..145 4-2 Experimental Section………………………………………………….………150 4-3 Results and Discussion………………………………………………..……….154 Synthesis……………………………………………………………….………..154 Mesogenic Properties…………………………………………………...………157 4-4 Conclusions…………………………………………………………………….161 4-5 References…………………………………………..………………………….162 Chapter 1-Index of Figures, Tables, and Schemes Figure 1. 1 left) the structure of GaQ2L, right) the spectrum of emission GaQ2Lfilm spin coated onto quartz. Solid line: emission ( ex= 370 nm; on the right) and excitation ( em= 515 nm; on the left)spectra of GaQ2Lin dichloromethane solution. Dotted line: emission ( ex= 370 nm)……………………………3 Figure 1. 2 Diagram showing the selective atomic labeling of PtIIcomplex Ptda4 and the inter-molecular stacking interaction; selected bond lengths: Pt-N1 = 2.026(3), Pt-N2 = 1.955(3), Pt-N4 = 2.028(3), Pt-N5 = 1.994(3), Pt‧‧‧Pt = 3.258 Å; boangles: N1-Pt-N2 = 79.18(13), N1-Pt-N4 = 178.75(12), N2-Pt-N5 = 177.15(13), and N4-Pt-N5 = 79.08(13)…………..………………5 Figure 1. 3 Optical textures of Colr amd Colh mesophases from Ptda4. Micrographs from heating process: left) Colr at 180 ˚C, (right) Colh at 264 ˚C. Samples were sandwiched between glass slides and viewed through crossed polarizer…………………………………………………………………..6 Figure 1. 4 Powder X-ray diffraction pattern of Ptda4 at 200 ˚C showed a Colr mesophas…………………………………………………………………..9 Figure 1. 5Powder X-ray diffraction pattern of Ptda4 at 300 ˚C showed a Colh mesophase………………………………………………………………….....9 Figure 1.6 Powder X-ray diffraction pattern of Ptda6 at 200 ˚C showed a Colh mesophase……………………..……………………………………………..10 Figure 1. 7 Powder X-ray diffraction pattern of Ptda8 at 250 ˚C showed a Colh mesophase……………………………………………………………………10 Figure 1.8Powder X-ray diffraction pattern of Ptda12 at 200 ˚C showed a Colh mesophase……………………………………………………………..…….11 Figure 1. 9a) UV/Vis absorption (> 430 nm) and emission spectra (< 450 nm) of complexes Ptda4(■), Ptda6(○), Ptda8(▲), and Ptda12(◇) in CH2Cl2. Note that the normalized emission spectra were acquired in degassed CH2Cl2 and were found to be superimposable…………………………………………..…12 Figure 1. 10 UV/Vis absorption (< 650 nm) and emission spectra (< 525 nm) of complexes Ptda4(■), Ptda6(○), Ptda8(▲), and Ptda12(◇) in neat film at RT……………………………………………………………………..….13 Figure 1. 11 The core structure of the antisymmetric chainlike architecture of a Ptda4 complexes after casting into a thin film; nitrogen atoms are omitted for clarity…………………………………………………………………..….14 Figure 1. 12 Temperature-dependent emission spectra of a neat thin film of Ptda12....14 Table 1. 1 The mesophases formed by compounds with 3,4,5-tris(hexadecyloxy benzoyloxy ligands depending on the number and the distribution of chains. [7b]…………………………………………………………………………3 Table 1. 2 Phase behaviors of Ptdax complexes………………………………5 Table 1. 3 X-ray diffraction data of Pt(II) metal complexes……………………..7 Chapter 3-Index of Figures, Schemes, and Tables Figure 3. 1 The phase transition chart of series 1N1,x with different mesogenic properties at cooling process……………………………………………….86 Figure 3. 2 Optical micrographs of compound 1N1,4 at cooling process, 193 ºC, black part presented homeotropic result, nematic texture. Scale bar: 50 m……87 Figure 3. 3 Optical micrographs of compound 1N1,4 at cooling process, 165 ºC sandwiched between glass slides between cross polarizers. Scale bar: 50 m.87 Figure 3. 4 Optical micrograph of compound 1N1,6 at cooling process, 143 ºC sandwiched between glass slides between cross polarizers. Scale bar: 50 m..88 Figure 3. 5 Optical micrograph of compound 1N1,12 at cooling process, 48 ºC sandwiched between glass slides between cross polarizers. Scale bar: 50 m..88 Figure 3. 6 The phase transition chart of 1N2,x and 1EN2,x with columnar mesogenic properties………………....…………………………………………………..90 Figure 3. 7 Optical micrograph of compound 1N2,6 at cooling process, 148 ºC sandwiched between glass slides between cross polarizers. Scale bar: 50 m..88 Figure 3. 8 Optical micrograph of 1N2,8 at cooling process, 100 ºC sandwiched between glass slides between cross polarizers. Scale bar: 50 m………………………91 Figure 3. 9 Optical micrograph of compound 1EN2,4 at cooling process, 210 ºC sandwiched between glass slides between cross polarizers. Scale bar: 50 m. (Heated to 230 ºC then cooled down to 195 ºC for 5 times.)………………..92 Figure 3. 10 Optical micrograph of compound 1EN2,8 at cooling process 155 ºC sandwiched between glass slides between cross polarizers. Scale bar: 50 m. (Heated to 190 ºC then cooled down to 100 ºC for 6 times.)…………………92 Figure 3. 11 Optical micrograph of compound 1EN2,12 at cooling process, 155 ºC sandwiched between glass slides between cross polarizers. Scale bar: 50 m.90 Figure 3. 12 The phase transition chart of XN1,6, XMN1,6 and 3N1,12 with different mesogenic properties…………………………………………………………94 Figure 3. 13 Optical micrograph of compound 2MN1,6 at cooling process, 100 ºC sandwiched between glass slides between cross polarizers. Scale bar: 50 m..95 Figure 3. 14 Optical micrograph of compound 3N1,6 at cooling process, 110 ºC sandwiched between glass slides between cross polarizers. Scale bar: 50 m95 Figure 3. 15 Optical micrograph of 3N1,12 at cooling process, 165 ºC sandwiched between glass slides between cross polarizers. Scale bar: 50 m……………..96 Figure 3. 16 The phase transition chart of 1N1,12 and 3N1,12 with columnar mesogenic properties………………………………………………………..98 Figure 3. 17 Optical micrograph of compound 2PN2,6 at cooling process, 210 ºC sandwiched between glass slides between cross polarizers. Black part presented thermal decomposed result. Scale bar: 50 m. (Heated to 225 ºC then cooled down to 200 ºC for 1 time. 70% of area has been decomposed)..98 Figure 3. 18 Optical micrograph of compound 3N2,12 at cooling process, 121 ºC sandwiched between glass slides between cross polarizers. Scale bar: 50 m..99 Figure 3. 19 contact preparation of 1N1,12 and deionized water at 48 °C, 50 m. A) heating process. B) cooling process………………………………………101 Figure 3. 20 50% deionized water and compound 1N1,12 at 48 °C, Scale bar: 50 m cooling proces……………………………………………………………..103 Figure 3. 21 75% deionized water and compound 1N1,12 at 48 °C, Scale bar: 50 m cooling process…………………………………………………..…………103 Figure 3. 22 PXRD results of 1N1,4 in nematic mesogenic phase……………..…105 Figure 3. 23 PXRD results of 1N1,4 in columnar mesogenic phase………………….106 Figure 3. 24 Representation of lattice rectangular columnar……………………….107 Figure 3. 25 PXRD stacking patterns of 1N1,12 with 0% deionized H2O at 45, 50 and 53 ºC at second cooling run………………………………………………..109 Figure 3. 26 PXRD stacking patterns of 2MN1,6 at second cooling run………111 Figure 3. 27 PXRD stacked pattern of 2PN2,6 at second cooling run………………113 Figure 3. 28 PXRD stacking patterns of 3N1,6 at second cooling run……………116 Figure 3. 29 PXRD stacking patterns of 3N2,12 at second cooling run……………119 Figure 3. 29 PXRD stacking patterns of 3N2,12 at second cooling run…………..116 Figure 3. 30 Proposed energy levels in polar and non-polar solvents………………122 Figure 3. 31 The UV-vis and fluorescence spectra of 1N1,12 with varied solvents…123 Figure 3. 32 Fluorescence results of compound 1N1,12 with varied metal ions. Zoom in part showed the spectra of 1N1,12 with W6+ and Pd2+ metal ions…124 Figure 3. 33 Fluorescence results of 1N1,12 with varied equivalents of Hg2+ metal ion………………………………………………………………………….125 Figure 3. 34 Fluorescence results of 1N1,12 with varied equivalents of Zn2+ metal ion……………………………………………………………………..…126 Figure 3. 35 Fluorescence results of 1N1,12 with varied acids. The inset colors showed the 1N1,12 in differnet acids under UV light, = 365 nm……………………127 Figure 3. 36 Fluorescence results of 3N1,12 with varied solvents………….129 Figure 3. 37 Fluorescence results of 3N1,12 with varied metal ions. The zoom in part showed the highest emission signals of 478 nm………………..130 Figure 3. 38 Fluorescence results of titrated a) 1N1,12 and b) 3N1,12 with W6+ metal ion in DMSO, respectively……………………………………..131 Figure 3. 39 Fluorescence results of titrated a) 1N1,12 and b) 3N1,12 with W6+ metal ion in DMF, respectively…………………………………………132 Figure 3. 40 Fluorescence results of 1N1,12 and 3N1,12 titrated with TFA results, respectively……………………………………………………………….133 Figure 3. 41 The sorts of net dipole moment of 11N1,12 and 3N1,12. Red narrow composed of pyridyl and phenyl groups and blue narrow composed of two phenyl groups……………………………………………………………..134 Figure 3. 42 Molecular orbital plots of simplified structure of 11N1,12 and 3N1,12. Caculated by Spartan (B3LYP/6-31G*). For compound 11N1,12, the LUMO located on the pyridyl group…………………………………………..135 Chapter 4-Index of Figures, Schemes, and Tables Figure 4. 1 The single X-ray diffraction structure of the CO2-incorporated product. 6a…………….……………………………………………………………..142 Figure 4. 2 Optical micrograph of C2OC8, sandwiched between glass slides between cross polarizers, on cooling at 57 ºC. Scale bar: 50 m……..…155 Figure 4. 3 Optical micrograph of EC2OC12, sandwiched between glass slides between cross polarizers, on cooling at 99 ºC. Scale bar: 100 m…….155 Figure 4. 4 CD spectra of neat EC2OC12 showing the negative Cotton effect. The neat sample was sandwiched between glass slides and spectra of 8 different spots of the slide were taken……………………………………………..156 Scheme 4. 1Reaction mechanism of propargylic alcohol with CO2.6………………142 Scheme 4. 2 Discotic mesogens with secondary alcohol moiety…………….……...150 Scheme 4. 3 Intended synthetic route to achieve inducing a chiral center onto a discogen……………………………………………………………………..151 Scheme 4. 4 The chiral moiety obtained from propargylic alcohol by thesilver-catalysed CO2 incorporation………………………………….…………151 Scheme 4. 5 The final structure generating from Sonogashira reaction with the chiral moiety and penta(phenylethyl)benzene………………………………..…152 Table 4. 1 The examination of various conditins of silver acetate and a chiral Schiff base ligand.6b……………………………………………………..…..143 Table 4. 2 Thermal behavior of cyclic carbonates derivatives and their precursors…………………………………..……………………………....154 |
參考文獻 |
1. (a) Vorlander, D. Z., Phys. Chem. 1923, 105, 211-254; (b) Ebert, M.; Jungbauer, D. A.; Lleppinger, R.; Wendorff, J. H.; Kohne, B.; Praefcke, K., Liq. Cryst. 1989, 4, 53-67. 2. (a) Krigbaum, W. R.; Poiroer, J. C.; Costello, J. M., Mol. Cryst. Liq. Cryst. 1973, 20, 133-135; (b) Chandrasekhar, S., Curr. Sci. 1978, 47, 523-563; (c) Omenat, A.; Ghedini, M., Chem. Commun. 1994, 1309-1395. 3. Serrano, J. L. 1996. 4. (a) Kaharu, T.; Matsubura, H.; Takahashi, S., J. Mater. Chem. 1991, 1, 145-146; (b) Kaharu, T.; Matsubura, H.; Takahashi, S., J. Mater. Chem. 1992, 2, 43-47. 5. Yoshio, M.; Mukai, T.; Kanie, K.; Yoshizawa, M.; Ohno, H.; Kato, T., Chem. Lett. 2002, 320-321. 6. (a) Kaharu, T.; Tanaka, T.; Sawada, M.; Takahashi, S., J. Mater. Chem. 1994, 4, 859-865; (b) Takahashi, S.; Kaharu, T., Chem. Lett. 1992, 1515-1516. 7. (a) Galerne, Y., Mol. Cryst. Liq. Cryst. 1988, 165, 180-184; (b) Ghedimi, M.; Pucci, D., J. Organomet. Chem. 1990, 395, 105-112. 8. Kumar, S.; Varshney, S. K., Liq. Cryst. 2001, 28, 161-163. 9. Mori, H.; Itoh, Y.; Nishiura, Y.; Nakamura, T.; Shinagara, Y., Jpn. J. Appl. Phys. 1997, 36, 143-147. 10. (a) Kohne, B.; Praefcke, K., Chimia 1987, 41, 196-198; (b) Marguet, S.; Markovitsi, D.; Goldmann, D.; Janietz, D.; Praefcke, K.; Singer, D., J. Phys. Chem. 1993, 97, 1358-1361; (c) Praefcke, K.; Kohne, B.; Gutbier, K.; Johnen, N.; Singer, D., Liq. Cryst. 1989, 5, 233-249; (d) Praefcke, K.; Kohne, B.; Gutbier, K.; Johnen, N.; Singer, D., Liq. Cryst. 1990, 29, 177-179. 11. (a) Kato, T.; Mizoshita, N.; Kishimito, K., Angew. Chem. Int. Ed. 2006, 45, 38-68; (b) Sawamura, M.; Kawai, K.; Matsuo, Y.; K., K.; Kato, T.; Nakamura, E., Nature 61 2002, 419, 702-705; (c) Gin, D.; Smith, R.; Deng, H.; Leising, G., Synth. Met. 1999,101, 52-55; (d) Kosonen, H.; RuoKolainen, J.; Knaapila, M.; Torkkeli, M.; Jokela, R.; Serimaa, G.; Bras, W.; Monkman, A. P.; Ikkala, O., Macromolecules 2000, 33, 8671-8675; (e) Mindyuk, O. Y.; DStetzer, M. R.; Heiney, P. A.; Nelson, J. C.; Moore, J. S., Adv. Mater. 1998, 10, 1363-1366; (f) Kishimoto, K.; Yoshio, M.; Mukai, T.; Yoshizawa, M.; Ohno, H.; Kato, T., J. Am. Chem. Soc. 2003, 125, 3196-3197; (g)Yoshio, M.; Kato, T.; Mukai, T.; Yoshizawa, M.; Ohno, H., Mol. Cryst. Liq. Cryst. 2004, 413, 2235-2244; (h) Lee, H.-K.; Lee, H.; Ko, Y. H.; Chang, Y. J.; Oh, W.-C.;Zin, W.-C.; Kim, K., Angew. Chem. Int. Ed. 2001, 40, 2669-2671; (i) Hoshino, K.;Yoshio, M.; Mukai, T.; Kishimoto, K.; Ohno, H.; Kato, T., J. Polym. Sci. Part A2003, 41, 3486-3492; (j) Mukai, T.; Yoshio, M.; Kato, T.; Ohno, H., Chem. Lett.2004, 33, 320-321; (k) Mukai, T.; Yoshio, M.; Kato, T.; Ohno, H., Chem. Lett. 2005, 34, 442-443.1. Wilson, J. N.; Bunz, U. H. F., J. Am. Chem. Soc. 2005, 127, 4124-4125. 2. (a) Marsden, J. A.; Miller, J. J.; Shirtcliff, L. D.; Haley, M. M., J. Am. Chem. Soc. 2005, 127, 2464-2476; (b) Marsden, J. A.; O'Connor, M. J.; Haley, M. M., Org. Lett. 2004,6, 2385-2388. 3. Pak, J. J.; Weakley, T. J. R.; Haley, M. M., J. Am. Chem. Soc. 1999, 121, 8182-8192. 4. (a) Tykwinski, R. R.; Diederich, F., Liebigs. Ann. Recl. 1997, 649-661; (b) Zhao, Y. M.; Tykwinski, R. R., J. Am. Chem. Soc. 1999, 121, 458-459; (c) Eisler, S.; Tykwinski, R. R., J. Am. Chem. Soc. 2000, 122, 10736-10737; (d) Zhao, Y. M.; Ciulei, S. C.; Tykwinski, R. R., Tetrahedron Lett. 2001, 42, 7721-7723; (e) Gisselbrecht, J. P.; Moonen, N. P.; Boudon, C.; Nielsen, M. B.; Diederich, F.; Gross, M., Eur. J. Org. Chem. 2004, 2959-2972. 5. (a) Wilson, J. N.; Josowicz, M.; Wang, Y. Q.; Bunz, U. H. F., Chem. Commun. 2003, 2962-2963; (b) Wilson, J. N.; Windscheif, P. M.; Evans, U.; Myrick, M. L.; Bunz, U. H. F., Macromolecules 2002, 35, 8681-8683; (c) Wilson, J. N.; Smith, M. D.; Enkelmann, V.; Bunz, U. H. F., Chem. Commun. 2004, 1700-1701; (d) Wilson, J. N.; Hardcastle, K. I.; Josowicz, M.; Bunz, U. H. F., Tetrahedron Lett. 2004, 60, 7157-7167. 6. Woo, H. Y.; Hong, J. W.; Liu, B.; Mikhailovsky, A.; Korystov, D.; Bazan, G. C., J. Am. Chem. Soc. 2005, 127, 820-821. 7. (a) Tolosa, J.; Solntsev, K. M.; Tolbert, L. M.; Bunz, U. H. F., J. Org. Chem. 2010, 75, 523-534; (b) Wagner, S.; Brodner, K.; Coombs, B. A.; F., B. U. H., Eur. J. Org. Chem. 2012, 2237-2242; (c) Seehafer, K.; Bender, M.; Bunz, U. H. F., Macromolecules 2014, 47, 922-927; (d) Seehafer, K.; Bender, M.; Schwaebel, S. T.; Bunz, U. H. F., Macromolecules 2014, 47, 7014-7020. 8. (a) Martınez, R.; Espinosa, A.; Tarraga, A.; Molina, P., Tetrahedron Lett. 2008, 64, 2184-2191; (b) Devaraj, S.; Saravanakumar, D.; Kandaswamy, M., Sens. Actuator. B 2009, 136, 13-19; (c) Elanchezhian, V. S.; Kandaswamy, M., Inorg. Chem. Commun. 2009, 12,161-165. 9. (a) Goze, C.; Ulrich, G.; Charbonniere, L.; Cesario, M.; Prangae, T.; Ziessel, R., Chem. Eur. J. 2003, 9, 3748-3755; (b) Cao, Y.-D.; Chen, C.-F.; Huang, Z.-T., Tetrahedron Lett. 2003, 44, 4751-4754; (c) Jiang, W.; Fu, Q.; Fan, H.; Wang, W., Chem. Commun. 2008, 259-267; (d) Hung, C.-H.; Chang, G.-F.; Kumar, A.; Lin, G.-F.; Luo, L.-Y.; Ching, W.-M.; Diau, 139E. W.-G., Chem. Commun. 2008, 978-980. 10. (a) Nolan, E. M.; Lippard, S. J., Acc. Chem. Res. 2009, 42, 193-203; (b) Tyrala, E. E.; Brodsky, E. L.; Auerbach, V., Am. J. Clin. Nutr. 1982, 35, 542-552; (c) Narli., I.; Kiralp, S.; Toppare, L., Anal. Chim. Acta. 2006, 572, 25-31. 11. (a) Bull, P. C.; Cox, D. W., Trends Genet. 1994, 10, 246-252; (b) Schaefer, M.; Gitlin, G. D., Am. J. Physiol. 1999, 276, 311-314; (c) Frederickson, C. J.; Koh, J.-Y.; Bush, A. I., Nat. Rev. Neurosci. 2005, 6, 449-462; (d) Harris, H. H.; Pickering, I. J.; George, G. N., Science 2003, 301, 1203-1205. 12. (a) Vallee, B. L.; Falchuk, K. H., Psychol. Rep. 1993, 73, 79-84; (b) Sensi, S. L.; Canzoniero, L. M.; Yu, S. P.; Ying, H. S.; Koh, J. Y.; Kershner, G. A.; Choi, D. W., J. Neurosci. 1997, 17, 9554-9564; (c) Coleman, E., Curr. Opin. Chem. Biol. 1998, 2, 222-234; (d) Lim, N. C.; Freake, H. C.; Brukner, C., Chem. Eur. J. 2005, 11, 38-49. 13. (a) Xu, Z.; Yoon, J.; Spring, R. D., Chem. Soc. Rev. 2010, 39, 1996-2006; (b) Lee, H. G.; Lee, J. H.; Jang, S. P.; Park, H. M.; Kim, S.; Kim, Y.; Kim, C.; Harrison, R. G., Tetrahedron Lett. 2011, 67, 8073-8088; (c) Kimura, E.; Koike, T., Chem. Soc. Rev. 1998, 27, 179-184. 14. (a) Renzoni, A.; Zino, F.; Franchi, E., Environ. Res. 1998, 77, 68-72; (b) Boening, D. W., Chemosphere 2000, 40, 1335-1351. 15. Harada, M., Crit. Rev. Toxicol. 1995, 25, 1-24. 16. Metivier, R.; Leray, I.; Valeur, B., Chem. Commun. 2003, 20, 996-997. 17. Battistuzzi, G.; Borsari, M.; Menabue, L.; Saladini, M.; Sola, M., Inorg. Chem. Commun. 1996, 35, 4329-4347. 18. Chandrasekhar, S.; Sadashiva, B. K.; Suresh, K. A., Pramana 1977, 9, 471-480. 19. Demus, D.; Goodby, J.; Gray, G. W.; Spiess, H.-W.; Vill, V.; Boden, N.; Movaghar, B. Handbook of Liquid Crystals. Wiley-VCH, Weinheim: 1998; Vol. 2B. 20. Nelson, J., Science 2001, 293, 1059-1060. 21. Percec, V.; Glodde, M.; Bera, K. T.; Miura, Y.; Shiyanovskaya, I.; Singer, K. D.; Balagurusamy, V. S. K.; Heiney, P. A.; Schnell, I.; Rapp, A.; Spies, H.-W.; Hudson, S. D.; Duan, H., Nature 2002, 419, 384-387. 22. Mende, L.; Fechtenkctter, A.; Mullen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D., Science 2001, 293, 1119-1122. 140 23. (a) Kim, J. Y.; Bard, A., J. Chem. Phys. Lett. 2004, 383, 11-15; (b) Fox, M. A.; Grant, J. V.; Melamed, D.; Torimoto, T.; Liu, C.; Bard, A., J. Chem. Mater. 1998, 10, 1771-1776; (c) Gregg, B. A.; Fox, M. A.; Bard, A. J., J. Phys. Chem. 1990, 94, 1586-1598. 24. (a) Harrison, D. J.; Fluri, K.; Seiler, K.; Fan, Z.; Effenhauser, S. C.; Manz, A., Science 1993, 261, 895-897; (b) Christopher, A. H.; Sanders, K. M. J., J. Am. Chem. Soc. 1990, 112, 5525-5534. 25. (a) Engelhart, U.; Lindner, J. D.; Tverskoy, B. O.; Rominger, F.; Bunz, U. H. F., J. Org. Chem. 2013, 78, 10832-10839; (b) Spitler, L. E.; Laura, D. S.; Michael, M. H., J. Org. Chem. 2007, 72, 86-96. 1. Choi, T. S. J.-C.; Yasuda, H., Chem. Rev. 2007, 107, 2365-2387. 2. (a) Yeung, C. S.; Dong, V. M., J. Am. Chem. Soc. 2008, 130, 7826-7827; (b) Ochiai, H.; Jang, M.; Hirano, K.; Yorimitsu, H.; Oshima, K., Org. Lett. 2008, 10, 2681-2683; (c) Boogaerts, I. F.; Nolan, S. P., Chem. Commun. 2011, 47, 3021-3023. 3. (a) Fujihara, T.; Xu, T.; emba, K. S.; Terao, J.; Tsuji, Y., Angew. Chem. Int. Ed. 2011, 50, 523-527; (b) Zhang, W.-Z.; Li, W.-J.; Zhang, X.; Zhou, H.; Lu, X.-B., Org. Lett. 2010, 12, 4748-4751. 4. (a) Shi, M.; Nicholas, K. M., J. Am. Chem. Soc. 1997, 119, 5057-5058; (b) Correa, A.; Martin, R., J. Am. Chem. Soc. 2009, 131, 15974-15975; (c) Aoki, M.; Kaneko, M.; Izumi, S.; Ukai, K.; Iwasawa, N., Chem. Commun. 2004, 2568-2569. 5. Uka, K.; Aoki, M.; Takaya, J.; Iwasawa, N., J. Am. Chem. Soc. 2006, 128, 8706-8707. 6. (a) Yamada, W.; Sugawara, Y.; Cheng, H. M.; Ikeno, T.; Yamada, T., Eur. J. Org. Chem. 2007, 2604-2067; (b) Yoshida, S.; Fukui, K.; Kikuchi, S.; Yamada, T., J. Am. Chem. Soc. 2010, 132, 4072-4073; (c) Kikuchi, S.; Yoshida, S.; Sugawara, Y.; Yamada, W.; Cheng, H.-M.; Fukui, K.; Sekine, K.; Iwakura, I.; Ikeno, T.; Yamada, T., Bull. Chem. Soc. Jpn. 2011, 84, 698-717; (d) Kikuchi, S.; Sekine, K.; Ishida, T.; Yamada, T., Angew. Chem. Int. Ed. 2012, 51, 6989-6992. 7. (a) Kato, T.; Mizoshita, N.; Kishimoto, K., Angew. Chem. Int. Ed. 2006, 45, 38-68; (b) M.Saez, I.; Goodby, J. W., J. Mater. Chem. 2005, 15, 26-40; (c) Tschierske, C.; Annu., R., Prog. Chem. Sect. C 2001, 97, 191-267. 8. (a) Praefcke, K.; Kohne, B.; Singer, D., Angew. Chem. Int. Ed. 29, 1990, 177-179; (b) Praecfcke, K.; Singer, D.; Gundogan, B.; Gutbier, K.; Langner, M., Ber. Bunsenges. Phys. Chem. 1993, 97, 1358-1361; (c) Marguet, S.; Markovitsi, D.; Goldmann, D.; 163 Janietz, D.; Praefcke, K.; Singer, D., J. Chem. Soc. Faraday Trans. 1997 93, 147-155. 9. (a) Kumar, S.; Varshney, K., Angew. Chem. Int. Ed. 2000, 39, 3140-3142; (b) Kumar, S.; Varshney, S. K.; Chauhan, D., Mol. Cryst. Liq. Cryst. 2003, 396, 241-250. 10. (a) Xu, Y.; Jiang, H.; Zhang, Q.; Wang, F.; Zou, G., Chem. Commun. 2014, 50, 365-367; (b) Varshneya, S. K.; Nagayamab, H.; Takezoeb, H.; Prasada, V., Liq. Cryst. 2009, 36, 1409-1415; (c) Varshney, S. K.; Prasad, V.; Takezoe, H., Liq. Cryst. 2011, 38, 53-60; (d) M., H., Chem. Soc. Rev. 2007, 36, 2070-2095. |
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